


Mistress Skylar, the Shota-Loving Shemale Sissy

by Feckless_Git01



Category: Original Work
Genre: Anal Sex, Big Ass, Cock Slut, Cock Worship, Deepthroat, Dirty Talk, F/M, Felching, Huge balls, Hung Shota, Other, Shemale, Shotacon, Triple Anal Penetration, big tits, blowjob, huge cock, sissy
Language: English
Status: In-Progress
Published: 2020-06-05
Updated: 2020-06-05
Packaged: 2021-03-03 23:22:38
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 6,150
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24553834
Author URL: https://archiveofourown.org/users/Feckless_Git01/pseuds/Feckless_Git01
Summary: In a lonely house, far from the eyes of many, is a person. A person who loves little boys. Little boys with big, thick dicks. And they lover her too, especially when they get to fuck her. Join the adventures of Mistress Skylar, the Shota-Loving Shemale Sissy and her trio of boy toys as they suck and fuck their time away.(Pretty heavily inspired by the works of SlutWriter, who is an absolute MASTER of sexual depravity. Can't reach his level of work, but this is just my attempt at trying. Plus, I want to write something shota related, and I like the ideas of sexually active young boys with big dicks owning a taller, curvy shemale with a small dick)
Comments: 11
Kudos: 45





	Mistress Skylar, the Shota-Loving Shemale Sissy

Every city, every town, in every country in all the world has them. From Tokyo to Moscow, London to New York, everywhere has the them; areas of affordable housing, built by the local government to house the overflow of the urban centres. Near uniform in appearance, usually drab colours though often times given a coat of paint to be more ‘uplifting’ to the populace and the residents.

The Projects, they’re called in some places in America. In Britain, they’re simply called Council Estates. Sometimes they’re a full high rise apartment, sometimes, they’re just a smattering of two storey houses around a cul-de-sac.

Stereotyped, oft times unfairly, sometimes unfortunately truly, as being dens of drug sellers and doers, women of ill-repute and children, mainly young boys or teens, who are the epitome of the delinquent.

Many times, those stereotypes are false. Often times, the latter ones are proven oh-so true.

* * *

“Fuck, I am bored!”

The exclamation into the mid-morning air from young, 10 year old boy was not all that out of the ordinary in Grace Avenue. Bobby Archer and his ‘gang’ of friends (well… two plus one hardly counts as a gang, but that’s how Bobby and the others liked to call themselves) were skipping yet another day of school, though it was Friday so hardly anyone really cared if they turned up or not. Plus, it was a summer’s day, so it was too warm to spend time in either school or home.

Sitting on the front porch of his house, Bobby stretched out his legs, skinny but athletic from all boyhood activities. Wearing only a pair of woodland camouflage shorts and a pair of white trainers, the 10 year old did what nearly all young men did when it was too hot: went topless. A thin body, lithe with energy but still slightly plump with young childish fat, was free to the open air. A tan was beginning to form, turning his pale skin a light shade of brown. His blonde hair, cut short into a fashionable faux-hawk, sat above a round boyish face, and a pair of light blue eyes looked out at the world in annoyance. He was short, only 4 foot 5, but Bobby didn’t let that stop him getting into trouble, as the healed over scabs on his knees attested to

“Want to head to the arcade?” Asked Bobby’s first friend, Ewan McDonald. 10 years old, Ewan was the same height but slightly podgier than Bobby, with light brown hair, currently hidden by an Everton football club cap, and green eyes. Despite the heat, he was wearing a long sleeve t-shirt in white, and a pair of black three-quarter length shorts, although it was easy to see he was suffering from the heat too. His parents often joked it was their Scottish heritage that made them so intolerable of the heat. Whatever that meant.

“Too fucking far.” Bobby replied, not out of malic at Ewan, but just of annoyance at the day. It was too far and too hot to go to the arcade.

“Is she going to call us?” Bobby’s other friend asked from his position sitting crossed legged on the top step. Michael Evans, sometimes called Micky, the youngest of the group at 9 years old, he was also the shortest, standing at a full 4 foot in height. He was very skinny, with a full head of curly black hair on top, making him look like a paintbrush. Dressed in a pale blue sleeveless t-shirt and a pair of cream shorts, he was as uncomfortable in the heat as the others. “Think she’d let us use her pool?”

She. Her.

The three had been friends for a good few years now, but that friendship had taken on a whole other level with them meeting… Her.

“I don’t know, Micky.” Bobby said, tilting his head back to look up at the sky.

“Well, text her then!” Ewan exclaimed, excited at the dual prospect of going for a swim and of meeting Her again. It was an excitement Bobby shared too.

Reaching into his pocket, he pulled out a smartphone, one of the latest models of Samsung. It hadn’t been something Bobby’s single mother could afford. It had been a gift from Her. In fact, She gave all of them gifts too in some shape or form. Sometimes food, sometimes gadgets, sometimes toys, sometimes… other things. Scrolling through his list of contacts, Bobby looked at the list of names. There were really only three others, since he didn’t both putting his own mum’s onto it.

Ewan.

Micky.

Mistress Skylar.

That was how she’d introduced herself when the three had first met her, trying to find the football that Bobby had kicked too hard into her back garden. ‘Mistress Skylar’. She wasn’t bossy, nor mean to them, but if ever Bobby had to say what a mistress was, she was one.

Selecting the last name, Bobby let his fingers type away at the screen.

**My friends are hot. Can we use the pool?**

“I’ve asked her.” Bobby said. He kept his voice level, but inside his stomach, excitement broiled away. The following seconds ticked away like hours.

*Ding!* The sound of a text alert went off and he immediately snapped his attention back to his phone as he read the reply.

**Good boys should be in school.**

**But it’s a good thing that you three are such naughty young boys.**

**Come round the back. The door is unlocked.**

Bobby’s face lit up brightly as he stared at the message.

“Well?” Micky asked expectantly. “What did she say?”

Bobby pocketed the phone before he stood upright. Reaching down to his crotch, he adjusted the lump that formed in his shorts.

“She says the door is unlocked.”

The other two boys smiled at the news.

* * *

It took roughly fifteen minutes for the boys to go from Grace Avenue to Mistress Skylar’s home. It would have been quicker on their bikes, but Bobby knew that if he tried to get his bike, his mum would ask questions on where he was going and the main thing that Mistress Skylar had insisted on was secrecy. She made no lie that what the group was doing was illegal, but they all knew it was too good not to do. So the trio walked through a portion of Grace Avenue, cutting around a disused plot of land, and then across a field towards a single solitary house.

It was a big house, more like a small mansion than any other house the boys had seen. It was at least three stories high, with balconies sticking out of some windows to be able to catch the sun on each side of the side. Bobby and his friends knew what the balconies were specially made to let anyone on them see out to the fields around it without letting anyone outside see them. Extra privacy was given to the house by the huge wall around it. At least ten feet tall in stone, it was topped with a steel fence that stopped anyone outside grabbing onto it. It was decorated with various flowers and plants to make it look nice. Three gates were built into the wall, one to allow chosen people in by car from the front, another to let in deliveries from the rear. Bobby and his friends knew of the secret entrance to the side. Hidden away by cleverly positioned bushes and stonework was a simple looking wooden door. There was a keypad beside it, with a code that only Mistress Skylar knew, and one that Bobby and his friends knew. Though this time there was no need for the code, as the light above the pad was green, showing the door was unlocked.

Excitedly, the trio pushed open the door into a small but specially prepared room, one the boys had been in many times. Shelves lined one side of the room, marked as ‘clothes’ and currently filled with towels, while on the other, a waist high surface top was set into the wall. On top of that surface was drinks of various, non-alcoholic kinds. Pop, energy drinks, fruit juice, water. All were prepared for the three boys.

“Should we wipe ourselves down with the towels?” Ewan asked as he took his t-shirt off his head, thankful for the extra layer to come off.

Bobby replied with single bark of laughter as he undid the buttons of his shorts. “You know Mistress Skylar! She always likes us to be sweaty. Especially down there.”

‘Down there’ was revealed as Bobby removed his shorts and underwear in one go, letting his pre-pubescent crotch swing into the air. He was huge. Soft ten year old cock meat swung free from its confines, a full foot in length and the thickness of a man’s fist. Bare of hair at its base, it was accompanied by a pair of low-swinging balls the size of ripe grapefruits. Bobby would have easily put any grown man to shame, and his friends too for that matter. If both Micky and Ewan weren’t packing their own extra-long pieces of pre-teen cockmeat.

The heat in the room kicked up a notch, and so did the smell as the boys let their dicks out into the air. Undressed and their clothes put to the side, without a word said between them, the three boys stepped out of the room, naked and barefooted, and into the world on the other side of the door.

It was like a garden from a fairy tale book, Bobby had to admit to himself. Neatly trimmed rose bushes lined the walls, freshly and perfectly cut grass lined the sides of the white marble pathways the three boys walked across. Despite the heat, the stone was cool against their soles, so they walked unperturbed. No other person came out to them, to either accost them for their nakedness or even to talk to them. They were completely on their own as they walked the path that lead them to their destination. All that surrounded them was the scents and sounds of nature.

As they walked along the path, the sounds and smells around the trio of boys changed. The scent of rose bushes and cut grass was overtaken by the smell of pool chlorine, mixing to form an interesting aroma. The sound of birds was replaced slightly, the new sound almost duelling with the old as the boys approached their destination. There was music in the air, something soft and sultry. Loud enough to be heard, but not loud enough to compete with any voices.

Other sounds reached the boys’ ears, ones they were familiar with and ones that they enjoyed hearing. Ahead of them, hidden away by an extra hedge of rose bushes, came the sound of feminine grunting and moaning, and the slick sound of something large being pushed and pulled inside an anus.

“Oooh, yes!” Came a loud, slightly muffled but sultry voice. “Oh, fuck, mm! Yes! Fuck me with that giant fuck stick, you whore.”

The voice was one Bobby, Ewan and Micky had become familiar with in the last month, along with the sounds accompanying the voice, and it had all of their pre-teen cocks growing hard. Without a word, the trio pushed forward, going to the location in the hedge that the entryway was, their giant cocks leading the way.

And they saw her.

Lying on her stomach on a large sunbed, giant tits pancaked to the side, was Mistress Skylar. She was a goddess, especially lying naked on the chair, revealing her body to the world. Standing over six-feet in height, her body proportions were insane. Tits that were easily a KK-cup sat high and pert on her chest, while her ass was equally as large. Wide hips and thick thighs led down to long, discretely muscled legs, legs which were spread out wide as Mistress Skylar had her asshole plowed by a dildo over a foot in length and half that in thickness by a maid. Her head was down, pressed to the surface of the sunchair, a cascade of bright blonde hair hiding her features.

The maid, a young woman in her mid-twenties dressed in what could loosely be called a uniform, was fighting hard to force the dildo in and out of the Mistress’ asshole. Sweat sheened from her forehead and exposed arms as the maid worked at the dildo hard.

Neither of them had noticed the three boys yet.

“Mistress Skylar!” Micky called out excitedly, his childish nature fully at odds with the situation before him.

The maid stopped her dildo as she lifted her head. Confusion briefly appeared on her face, before it gave way to joy.

“Mistress, Bobby and his friends are here.” She said, her voice a lilting tone as she withdrew the dildo fully from the taller woman’s asshole, setting it down on the floor.

Raising her head, brushing away her hair, Mistress Skylar looked at the cause of the disturbance. Where normally annoyance would have been plain on her face at the intrusion, wide eye joy came to her face. Baby blue eyes twinkled as she looked at the three boys, her round face splitting into a grin as she moved her gigantic body to sit upright on the chair.

“Hello, boys!” Mistress Skylar said out loud, her eyes sweeping over the three boys, paying attention to their pre-pubescent bodies, especially their unnaturally giants cocks. “You three came her so quickly, I thought I’d have time for my exercises.”

Standing from the sunbed, pulling herself to her full height, Mistress Skylar walked towards the boys. Giant tits bounce up and down, large hips swayed back and forth, while her small, three-inch penis hung and swung limply from her crotch, testicles the size of grapes hung beneath and behind.

It had been one of the things that had shocked Bobby and his friends when they first met Mistress Skylar. She was rich, she was sexy, she was also, as she described herself, a ‘shemale sissy’. Not that that had ended up bothering the three boys when they first lost their virginities to her.

Squatting down, her knees closed, Mistress Skylar held out her arms. “Come and give me a hug, you lovely boys.”

Moving as one in a quick burst of speed, the three boys practically collided with the super-stacked sissy, her giants tits smushing against their torsos, all their combined sweat merging together to become a sticky layer. Giants cocks pushed against her skin, rubbing to the side across Mistress Skylar’s body as she hugged them. Her arms encircled the young boys, pulling them against her body before she craned her neck down to kiss Bobby on the lips. The kiss wasn’t a chaste kiss, like a mother would give their child, this kiss was lust filled. Pushing her tongue, Mistress Skylar penetrated Bobby’s mouth, moving her tongue around the confines of his mouth, making his cheeks bulge out. Releasing his lips, Mistress Skylar moved onto Ewan then Micky, her tongue repeating the same action on each boy before, with a spit filled *pop!*, she released each Micky’s mouth.

Her tongue, covered in the mixture of their spit, went back into her mouth, Mistress Skylar swallowing the mix and shuddering happily at the taste.

“Mmm.” She moaned out. “I love the taste of little boys.”

Releasing her hold on the boys, Mistress Skylar stood upright, her tits swinging slightly as they bounced at head height with the boys.

“So… what can I do for you three today?” She asked, putting her hands on her hips

“Can we swim in the pool?” Micky asked, the nine-year-olds childish exuberance completely at odds with the semi-erect cock hanging from his crotch.

Mistress Skylar tittered. “Of course you can, Micky. Just go right ahead. This place is as much yours as it is mine.”

With whoops of joy, Micky and Ewan sprung forward, giant cocks swinging and slapping against their balls as they rushed to the pool. In the style of young children, the pair jumped into the pool without hesitation, geysers of what splashing up from their entry. The action earned a giggle from Mistress Skylar and her maid.

“Mary,” The tall shemale said, addressing the maid. “Go and get the pool floats. Give them something extra to play with.”

“Of course, Mistress.” The maid said demurely, standing up from her position by the sunbed before moving off into the house. Which left Bobby and Mistress Skylar alone.

“And what about you, Bobby? Not going to join in?”

The blonde-haired boy looked at his friends before he looked back at the older, taller woman. He shook his head.

“No, the pool was Micky’s idea.” Stepping closer to her, Bobby reach forward and took a handful of one of Mistress Skylar’s tits, his fingers sinking into the flesh and drawing a moan from her. “Besides… I want you.”

Mistress Skylar moaned again as Bobby rubbed his hand over the flesh of her tit before she smiled happily at the ten-year-old.

“Oh, Bobby. You know just what you like. And what I like too.”

Reaching a hand down to rest against Bobby’s head, Mistress Skylar led Bobby to her sunbed. Bending over, she fiddled with the headboard, pushing it up so that was perfect for the boy to sit on. With a childish lack of aplomb, Bobby moved past the shemale and sat on the sunbed, letting his legs hang over the side and letting his cock stand out from his body. Half-hard now, Bobby’s cock measured an imposing foot and a half in length. Though from the smile on her face, Mistress Skylar was not scared at all.

“Oh, I love your giant, little boy dick.” The sissy said as she leant down in between Bobby’s legs, bringing her face level with his dickhead. Letting out her tongue, Mistress Skylar pushed forward and began to lap at the organ, her tongue running circles over the first-sized head. Pre-cum began to flow onto her tongue, sending another shudder through her body. Pushing forward, Mistress Skylar engulfed the cock in her thick lips, stretching them as she began to swallow the first few inches of Bobby’s cock. The effect on the young boy was immediate as the cock began to grow, enlarging and lengthening inside the shemale sissy’s mouth, pushing the head further down her throat. Before she ended up deepthroating the boy, Mistress Skylar moved her lips off the cock, spittle flying off the section her mouth was over, a near insignificant portion of his two-and-a-half foot cock. “Oh fuck,” The woman said, moving her onto the slick portion of Bobby’s cock and began to slow, gently, jack him off. “I can never get over how fucking big you are.”

Bobby smiled down at the shemale sissy as she worshipped his dick. Out of his friends, he was the one who most enjoyed sex with Mistress Skylar. Letting her jack off his dick, suck him off, take him in other ways. He loved them all.

“Oh, Mistress.” The maid called Mary said, walking past the older person on the sunbed, arms filled with various pool floats, as she began to lap at the untouched length of the pre-teens cock. “Are you going to be filming another video today?”

Not answering immediately, Mistress Skylar moved her head down, right between the boy’s legs before she pushed her face against Bobby’s balls. Smushing her face against the sweat-slick skin, pressing her face between his grapefruit sized orbs and breathed in deeply. _SNORRRT!_ The sound filled the air as Mistress Skylar deeply inhaled Bobby’s smell, her eyes rolling back in her head like an addict getting a fix. Moving her head off the boys testicles, a string of sweat and mucus dangling from her nose, Mistress Skylar looked at her maid as she ran her tongue to pick up the mix.

“No, not today, Mary. Although… I might have an idea for a video later on.”

Videos. That was how Mistress Skylar made her money, and why she was called Mistress Skylar. It was heavily illegal, but there was a market for people watching Mistress Skylar being fucked by pre-pubescent boys with giant cocks, and people across the world paid a lot of money to watch the videos, either live-streamed or pre-shot videos. Bobby and his friends were famous on the deep web.

The boy’s train of thought was interrupted as Mistress Skylar attached her tongue to his length again, drooling heavily before she moved her head upwards to the top of Bobby’s dick. Drool bubbled around the shemale’s tongue as she worshipped the giant length of cock-meat in front of her. Steadily, she moved upwards the tip, the leaking precum from the knobhead leaking down to increase the slipperiness on the organ. Holding onto the cock with both hands, like it was a precious lover, Mistress Skylar kissed, licked and slobbered over the organ, getting it nice and slick. Steadily, the shemale sissy moved up to the leaking cockhead.

“Yummy, yummy.” Mistress Skylar said absentmindedly as she licked up the increasing amount of pre-cum. Opening her mouth wide, she engulfed the knobhead in her maw then went even further as she swallowed half a foot of ten-year-old dickmeat. The thickness of Bobby’s cock bulged out her throat obscenely, though if the sissy shemale was in any discomfort, she wasn’t showing it. In fact, it was clear she was enjoying it. Her eyes were rolled into the back of her head, the white showing, as she began to properly fellate the cock in her mouth. She moved her head back, keeping the knobhead fast between her lips before she pushed forward again, sinking a whole foot of Bobby’s cock into her mouth.

GLLLRRK!

The sloppy sound of the shemale swallowing the cock filled the air, spittle and precum spurting from between her lips. Sloppy drool spilled down from between her lips as Mistress Skylar began to fellate the giant cock, a foot length of cock filling her throat as she bobbed her head up and down.

GLLLRK! GLLLRK! GLLLRK!

Bobby let out a groan of pleasure as his fingers intertwined into Mistress Skylar’s blonde locks, his hands fixed to her head as she bobbed up and down.

“Oooh, Mistress Skylar…”

“Hey! That’s not fair!” Ewan’s voice called out, making Bobby look at his friend. The other ten-year-old was standing in the shallow end of the pool, a trio of pool noodles in his hands, ready to be used to swim with. His own cock was now fully erect, the same two-and-a-half-foot monster that he shared with Bobby and Mickey. “You didn’t say anything about doing that with Mistress Skylar.”

“You guys just-ngh-said you-ngh-fuck-ngh-wanted to play in her pool!” Bobby retorted, his hands still on the shemale’s head as she swallowed more of his cock, over a foot-and-a-half of pre-teen boy dickmeat stuffing her gullet.

GLLLRK! GLLLRK! GLLLRK!

“But when all three of us are here,” Mickey spoke up, standing next to his friend, a hurt look on his face. “You know that we all have fun with her, at the same time! That’s the rule!”

“I know it’s the rule but...” Bobby’s train of thought was interrupted as he felt Mistress Skylar, two feet of cock in her mouth, slapping lightly on his thigh to get her attention. It wasn’t from discomfort or pain, that much was clear, since the shemale had swallowed the thick boycock many times before, deepthroating him and his friends easily. The tap was to get his attention.

Languidly, Mistress Skylar began to move her head back, twisting her head side to side, as she let the length of cockmeat slip from between her lips. Inch by inch of that gloriously sized cock was revealed to the air, slick with the leavings of the depraved shemale’s cock worship. The head slipped from her lips with a resounding *POP!* that flung spittle, throat-slime and pre-cum almost everywhere.

“Boy, stop it.” Mistress Skylar said pleadingly, her lips, shining from her blowjob, pouting as she spoke. “Friends shouldn’t fight, especially over someone like me. Bobby just wanted me to treat him, that’s all. But if you all want to do it… Bobby, honey, get off the sunbed for me.”

Without a word of protest, the ten-year-old vacated his seat on the sunbed, standing up as Mistress Skylar moved forward. Languidly, she crawled to the head to bed, her knees pushed up beneath her to let the boys see the full extent of her large, heart-shaped, cow-sized rear-end as she fiddled with the back of the sunbed, letting the headrest slip down. Mickey and Ewan had exited the pool, their bodies dripping with water and their cocks dripping with arousal at the sight. Mary the maid appeared between them, grasping a hand on to each of their dicks as she began to jack them off, slicking their lengths up right with an obscene amount of lube.

“You know slick and wet Mistress Skylar likes her fucks.” The older woman said, her nipples rigid and her pussy leaking with lust, as she jacked off the boys slowly. She went from head to base, making sure each boy’s cock was thickly and richly coated in a thick layer of the shining lubricant. The day was progressing much faster than either she or her Mistress had anticipated, but they knew the boys well, and this sort of thing was expected. So she worked slowly, making sure that both boys were lubed up right, but not brought to orgasm. That was Mistress Skylar’s job, and she let them go when Mistress Skylar gave the word “Ready!”

Sunbed set and rolling on to her back, Mistress Skylar lifted her legs up and backwards, her feet moving until they touched the sides of her head. It was one of her favourite positions when she had the boys around, putting her asshole on display, along with her insignificant dicklet. Fuck, it was a blessing from God that she ended up meeting these boys.

“Okay, boys!” She called out happily, looking at the three giant, erect, leaking cocks pointed directly at her asshole. “You know what to do! Fuck me like you mean it!”

Bobby stepped forward, his dick still leaking throat-slime, spittle and pre-cum, as it was pointed directly at Mistress Skylar’s winking asshole. It looked impossible, such a large cock fitting into such a small hole… but as Bobby sunk his head into it, Mistress Skylar was thankful that she’d been using her asshole for fun since she was ten too. In and in, the ten-year-old cock went, stretching out the hole sideways and stretching out her stomach lengthways. The cock travelled further, the thick head pressing through Mistress Skylar’s bowels before it pressed down against her prostate.

The shemale sissy’s dicklet spurted, the weak string of liquid that passed for cum splashing out onto her stomach. Mistress Skylar’s eyes crossed, and her mouth gaped open.

That was just one dick too…

The thud of Bobby’s hips colliding with Mistress Skylar’s signalled the full penetration of his two-and-a-half feet length cock into her bowels. Moving quickly, the boy climbed up her body, keep his cock in Mistress Skylar’s ass as he sat on top of her upturned hips, his crotch just touching her spasming dicklet.

“O-okay,” Mistress Skylar said, trying to fight through the pleasure. “E-Ewan? Y-you’re up next.”

The pudgy ten-year old stepped forward, his dick covered in an absolutely thick helping of lube, as he put a foot onto the sunbed. Slowly, Ewan pressed his cock against the shemale’s already filled hole. Such a fit would truly be impossible, but, as Ewan pressed his hips forward, Mistress Skylar’s asshole spread wide, accepting the extra intruder. There was a stretching sensation, no pain, but as Ewan’s cock pushed forward, it pressed Bobby’s cock down harder on to her prostate. The sissy let out a open mouthed, silent scream of pleasure as her dicklet fired again, more cum falling to rest against her stomach, a stomach that was now heavily stretched out by a pair of pre-pubescent cocks.

But they weren’t finished yet.

“M-Mickey!” Mistress Skylar called out. “Stick your giant donkey dick in me! Please, I need it!”

The youngest of the boys rushed forward, his cock, dripping heavily with lube, bouncing up and down as he moved closer. Putting a foot onto the sunbed and jostling quickly with Ewan for position, Mickey placed his cock on the other side of Bobby’s cock, forming a pyramid of pre-pubescent penis inside of the shemale sissy’s ass. Pressing his hips forward, Micky began to push his cock into Mistress Skylar’s bowels, but he was stymied by the two giant cocks already in her.

“Fuck me, boys!” Mistress Skylar called out, almost pleading with the boys as she gave into the pleasure. “Let Mickey get in there by fucking me!”

So that’s what the boys did. Slowly, Bobby and Ewan withdrew their cocks, their thickness pressing down on Mistress Skylar’s prostate again, as they pulled back to their knobheads. For his part, Mickey sank his length in, bottoming out easily inside of the shemale’s seemingly never-ending asshole. The three-fold penetration had Mistress Skylar’s prostate acting overtime. She was coming virtually non-stop, especially when Mickey withdrew his own cock and Bobby and Ewan sank theirs into her guts.

“F-fuck, yes!” Mistress Skylar called out, her tits bouncing along with her dicklet, the latter spraying out cum. “Yes! I love you boys! I love your fucking giant donkey dicks, and I love it when you fuck me with them!”

Bobby thrust downwards from his angle, spearing his cock deep into the sissy’s ass, as Ewan and Mickey found their own rhythms. They were able to penetrate her both at the same time, their thick dicks spreading her asshole wide, while Bobby thrust deep when the pair had withdrawn their cocks.

The sound was filled with the sloppy, wet clap of thick, wet cocks spearing open an asshole.

CLAP-CLAP-CLAP-CLAP-CLAP

It was the ultimate form of depravity: a sissy shemale in her early thirties, being fucked by three pre-pubescent boys with giant dicks at the same, her asshole stretched out to accommodate their girth. As they fucked her, Mistress Skylar’s stomach bulged out with each penetration, showing the path of each cock as it went through her bowels, lodging themselves near her diaphragm. Each thrust forward had her body jiggling, her ass rippling as her tits bounced, and her cock spewing each time,

“F-faster! Fuck me faster, boys! Breed your mistress’ slutty ass!” She called out, and the boys obliged.

CLAP!CLAP!CLAP!CLAP!CLAP!

The boys picked up speed, the sound of their fucking rising in tempo as they fucked Mistress Skylar. There was never a moment that a cock wasn’t in her ass, the long, bulging length of one pressing up through her stomach. Her prostate was being brutalized, the gland continually being pressed by the thick dicks, making Mistress Skylar orgasm non-stop.

“Y-yes!” She called out as she wrapped her arms around Bobby’s body, pulling him further down against her tits. “I-fuck-I fucking love you boys! You-fuck-You fill me better than anyone-fuck-ever has!”

The boy’s thrusting didn’t let up, Mistress Skylar’s words only encouraging them further. Their hips collided with her ass, sending thick ripples through the fat and the flesh. They didn’t let up as they fucked the older shemale sissy, their focus wholly intent on rutting her ass and breeding her as she had commanded.

Minutes ticked by and numberless thrusts too, and Mistress Skylar could feel their cocks begin to pulse and throb, the sure sign that they were ready to unleash their loads within her ass. Not that she could do or say anything, as her mind had gone blank with pleasure from repeated constant orgasms. Her stomach was now a sodden mess of leaking cum, the liquid trailing down her sides to fall to the sunbed below. The shemale’s eyes were unfocused, partially crossed, while drool came from her open mouth.

“F-fuck!” Bobby sounded off loudly as he kept thrusting. “I’m-I’m going to cum!”

“Me too!” Ewan and Mickey said at the same time, keeping up their thrusting.

Quickly, the boys matched their rhythms, all three pulling out their cocks to the head before thrusting in, bulging out Mistress Skylar’s stomach obscenely. Again and again, the bulge disappeared and reappeared as the boys fucked her.

Then, at the last minute, they slammed their cocks in deep and came inside of the shemale’s ass, three different cries of “I’m cumming!” signalling the boys orgasms. Even in her lust-addled mind, Mistress Skylar felt the urethras of the three mighty cocks bulge out before the tide of cum filled her bowls. Litres of cum were poured into her stomach, ballooning out her stomach obscenely. Each burst of cum was accompanied with an audible “SPLURCH!* as it filled up the shemale’s bowels with boy cum, and each load of cum set off Mistress Skylar in an orgasm, her own dicklet spurting out cum. The shemale couldn’t say anything, her mind so addled by pleasure and lust, so all she could do was make animalistic grunts and cries as she was filled with pre-teen boy cum.

The boys’ orgasms seemed to last minutes, the amount of cum filling Mistress Skylar so much that it looked like she was pregnant with octuplets, the pressure so much that it ended up backflowing from between the cock stuffed anus. It was bliss for all involved; the boys got to release their pent-up lust, and Mistress Skylar got to indulge her love for long, thick pre-teen boy dicks. She could feel their sweat slick skin pressing against her ass and stomach, and when she felt Bobby stick his tongue into her open mouth, it was on instinct that she closed her lips around it and suckled on it.

With grunts of effort, the boys finished cumming, shooting off the last bits of cum into Mistress Skylar’s belly. To Bobby, nearly resting on her stomach as he disengaged from the kiss, he found it to be like resting on waterbed. Looking at her face, the ten-year-old took in the expression on the shemale’s face: her eyes were unfocused, nearly rolled up to the whites, her mouth was wide open, and her tongue was hanging limp from one corner, a thick string of drool escaping down her cheek. Tears of joy and bliss rolled from her eyes, even as her lips moved into a smile.

She was in absolute bliss.

“Did you enjoy that, Mistress Skylar?” Bobby asked.

The shemale smiled, then moaned as she felt one of the cocks throb in her ass again, making her dicklet spurt out a trail of cum. The three boys were still hard as pillars of granite.

“Then let’s go for Round Two!” The blonde ten-year-old exclaimed happily, the other two boys echoing his exclamation excitedly.

Mistress Skylar couldn’t give a word in reply, her mind too addled and broken with pleasure. All she could do was moan whorishly as the boys began to fuck her ass again.

* * *

The sun had gone well past its noon-day zenith when Bobby Archer leant his shoulders back against the cool stone of the pool. He was seated in the shallow end, reclining on the specially built seats set into the edge of the pool, and he was really relaxing. He and the others had had a shower to remove the worst of the sweat and the cum from their young bodies, and Mary had prepared lunch for them too: beef burgers, onion rings and Pepsi. The trio were now fully relaxing in the pool.

“This is so much better than school.” Ewan said as he floated through the pool, being kept afloat by a trio of pool noodles, his own pool noodle hanging limp below him.

“I know, right?” Bobby replied, looking at his friend as he smiled. Across from him, Mickey was sitting on a seat by himself, letting his feet kick at the water absentmindedly. Turning his head, the nine-year-old smiled at his host.

“Thank you for letting us use your pool, Mistress Skylar.” He said innocently, his face smiling.

Reclining once again on the sunbed, the shemale, her stomach heavily distended by the absurd amount of boycum she’d been anally inseminated with, lifted a hand up to wave at the boys. Mistress Skylar was a mess: cum was leaking prodigiously from her stretched out asshole, even as her maid stuck her head in between the cheeks to slurp away at the delicious, warm white treat running from between the shemale’s ass. The shemale sissy was out of it, but she was in heaven.

Even through her lust addled mind, she hoped the boys would come back again. The triple-anal fucking would make a good video.


End file.
